


What a Drag

by TheAnnoyingAlien



Category: Political RPF - US 21st c.
Genre: Crack, Crossdressing, I Was Drunk When I Wrote This, I'm Sorry, M/M
Language: English
Status: Completed
Published: 2020-12-16
Updated: 2020-12-16
Packaged: 2021-03-10 18:08:11
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,440
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28101420
Author URL: https://archiveofourown.org/users/TheAnnoyingAlien/pseuds/TheAnnoyingAlien
Summary: Donald Trump is furious at his lawyer for how he’s handling the Mueller investigation, but Rudy Giuliani has a plan to get back into his boss’s good graces (and his pants). Posted in honor of Giuliani getting COVID.
Relationships: Donald Trump/Rudy Giuliani
Kudos: 2





	What a Drag

**Author's Note:**

> I started writing this in like 2018 as a joke then forgot about it and it’s been sitting unfinished until now, but after I heard that Giuliani got COVID I remembered that this existed and thought I might as well finish it to commemorate the occasion lol... back in 2018 I learned about that skit Giuliani did back when he was a mayor where he’s dressed in drag and flirting with Trump. The video made me laugh so hard my eyes teared up and I felt inspired (for better or worse) to write some cursed bullshit based on it. Anyways, sorry if there are any errors in this, I was kind of drunk when I finished and proofread it but enjoy this abomination and hopefully it makes you laugh and takes your mind off the COVID hellhole we’re living in.

“Take your hand off my ass, Donald.”

Donald Trump pouted, letting his hand slide off of the other man’s rear. “Come on, Rudy!” He whined. “Don’t tell me you don’t want it, because I know you do! You haven’t gotten any since your wife decided to divorce you!” His companion and lawyer, Rudy Giuliani, turned his nose up at him.

“We’ve got bigger things to worry about than blue balls,” Rudy huffed, “Like making sure Mueller doesn’t have any case against you.”

“You’re doing a pretty fucking shitty job at helping me with that,” Donald groused, “Some lawyer you are! You’re the worst lawyer I’ve ever had, and I’ve had plenty of them!”

“Then go ahead and call upon one of the others for help!” Rudy snapped, throwing his hands up in frustration. “But I bet none of them look as good in lipstick and heels as I do, and none of them can suck dick like I can!” He turned on his heel and sauntered out, leaving an angry, horny Donald alone in the Oval Office. Donald, realizing he wasn’t getting laid any time soon, muttered a string of curses and then went about his day as usual. The hours ticked by, the sun began to set, and soon it was well into the evening. Donald was still at his desk in the Oval Office, busy firing off late night tweets about the liberal media and building the wall instead of actually doing anything presidential. He threw in another few passive aggressive tweets about various other world leaders for good measure and tossed his phone aside on the desk. He was still incensed about Mueller’s continuing investigation and Rudy’s fumbling attempts to take the heat off of him, and creating controversy on social media only did so much to help him unwind. He liked Rudy, and he liked having him in his bed, but he was furious with the way he’d been handling the Mueller investigation. Sighing, Donald reached for the can of Diet Coke that had been sitting on his desk all day and cracked it open, taking a swig. There was a knock at the door, he slammed the can down on the desk and swore loudly, not wanting to be disturbed while he was sulking.

“What is it?” He called out. The door opened, and a middle aged woman slipped into his office, closing and locking the door behind her. She was dressed in a simple lavender gown that clung to her curves in a way that Donald found particularly delicious, and over this gown she wore a matching lavender shawl. She had platinum blonde hair styled in elegant waves, and she reached a gloved hand up to gently brush some of the waves away from her face, a face that, though heavily caked with makeup, was immediately recognizable to Donald as the face of his lawyer.

“Hello, Mister President.” Rudy greeted him, modulating his voice into a high pitched falsetto as he batted his eyelashes at Donald.

“Well hello there, Miss Giuliani,” Donald replied, grinning, “It’s been a while since I’ve last seen you.” Rudy gave a dainty giggle and trotted over to the desk, trying to not appear too wobbly in his high heels as he wiggled his hips in a way that he hoped was seductive. Judging by the intrigued look Donald was sporting, it seemed to be working. Rudy plopped himself down in Donald’s lap, drawing his arms around the president’s neck and locking eyes with him before leaning in until his lips nearly brushed against Donald’s ear.

“You poor dear,” Rudy purred, “You must be so frustrated with this whole investigation business.”

“Very, very frustrated!” Donald agreed, caressing Rudy’s thigh, “But that’s why you’re here, right? You’re gonna give me a hand?” Rudy lifted his head and flashed a coy smile at his boss.

“A hand, a mouth, an ass too if you want it,” He smirked, “Just say the word, and I’ll make it happen.” Donald grabbed Rudy by the chin and crushed their faces together in a rough kiss, plunging his tongue into the other man’s awaiting mouth. Donald trailed kisses along his lawyer’s jaw, down his neck, finally stopping to dive his face into Rudy’s fake cleavage. He was impressed by how realistic it felt; it was just like burying his face in the chests of the buxom porn stars he’d paid off to keep silent. Donald lifted his head from the fake boobs and reached up to stroke Rudy’s bottom lip with his thumb, grinning wickedly as they locked eyes.

“I know what I want next,” He leered, “Come on. On your knees.” Rudy obediently knelt in front of him, gloved fingers tracing over Donald’s crotch. He knew what Donald wanted and knew what to do, and that was exactly what he did. When he was finished, Rudy rose from between Donald’s legs, bleach blonde wig all messed up from Donald digging his fingers into it and lipstick smeared across his face. Rudy swallowed audibly and dragged one of his gloved hands across his lips to make himself a bit more presentable. Still keeping character, he frowned and gave Donald a playful swat on the thigh.

“Oh, you dirty boy, you!” He scolded his lover, “Donald, I thought you were a gentleman!”

“I can still be a gentleman,” Donald replied, “I know how to treat a lady.” He slid one of his hands up Rudy’s skirt, resting it atop the panties the man was wearing beneath. Color came to Rudy’s cheeks, though it wasn’t visible beneath the layers of caked on makeup he was wearing.

“Oh! Donald! But… I thought you wanted, you know…” He stammered, breaking character and using his normal, deeper voice now.

“Your mouth was so good I don’t even need you to give me your ass today,” Donald told him, “Now, Miss Giuliani, let me show you how I treat a lady.” Donald ducked his head underneath Rudy’s skirt, repaying the favor. When he was finished Donald emerged from the shroud of purple fabric and took a swig of Diet Coke to wash out his mouth. Rudy slumped back against the desk, legs still trembling from the aftershocks of bliss, and felt Donald grab hold of his arm.

“You’ll get Mueller off my ass, won’t you baby?” Donald purred against his ear.

“Of course!” Rudy replied in what he hoped was a confident tone to mask the unease he felt. “I’ll keep you in the clear!” Donald rewarded him with a kiss.

“Good. Now get out so you can keep working on that, but be discreet about it.” Rudy slipped his feet out of his high heels, scooped them up from the floor, and quietly crept off to make his exit. Unfortunately for him, as he was leaving the Oval Office, Mike Pence happened to be approaching it. Mike’s eyes widened as he caught sight of Rudy in all of his drag queen glory, and Rudy froze where he was, like a deer caught in the headlights in the vice president’s gaze. Mike regarded him for a moment, clearly confused and creeped out by his attire, then entered Donald’s office without a word as Rudy scampered off down the hall.

After the meeting with Pence-a meeting that mercifully did not include any interrogation over why his lawyer had been fleeing his office dressed as a woman-Donald decided to retire to his bedroom for the evening and do some hate watching of MSNBC. He pulled his phone out so he could live tweet about how horrible their fake news was as he waited for the next segment to start. The clock had struck eight, so Chris Hayes, noted Bernie Sanders ass kisser, was on for his hour.

“Breaking news,” Chris began, his face, which looked way too youthful for an almost forty year old man, lit up by the studio lights, “Donald Trump and Rudy Giuliani are having a clandestine affair, one that, according to an accidental phone call Giuliani made to us earlier, involves cross dressing roleplay.” Donald nearly choked on his Diet Coke as the network began playing a recording of the call, albeit censored slightly for television. Judging from where the recording began, Donald concluded that Rudy had been stashing his phone in one of the pockets in his dress and had most likely sat on it, inadvertently calling up the network as he’d made himself comfortable in Donald’s lap. Fuming with rage, Donald closed out of Twitter and dialed up a certain lawyer to vent his frustrations.

“RUDY.” Donald snarled into the phone. “YOU BUTT DIALED NBC AGAIN!”

The End


End file.
